Synthesis of Fluorinated Aminoalkylboronic Acids from Amphoteric α-Boryl Aldehydes

被引：6
|
作者：
Soor, Harjeet S. [1 ]
Diaz, Diego B. [1 ]
Burton, Katherine I. [1 ]
Yudin, Andrei K. [1 ]
机构：
[1] Univ Toronto, Dept Chem, 80 St George St, Toronto, ON M5S 3H6, Canada
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2021年 / 60卷 / 30期
基金：
加拿大自然科学与工程研究理事会;
关键词：
aminoalkylboronic acids; electrophilic fluorination; fluorine-containing boronic acids; alpha-boryl aldehydes; STEREOSELECTIVE-SYNTHESIS; NUCLEOPHILIC TRIFLUOROMETHYLATION; BORONIC ACIDS; INHIBITORS; LINCHPINS; BINDING;
D O I：
10.1002/anie.202104133
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Our ongoing search for underdeveloped functional group combinations has brought to light alpha-fluorinated aminoalkylboronic acids, a new class of molecules featuring the B-CF linkage. These compounds can now be generated from secondary amines and alpha-boryl aldehydes through electrophilic fluorination of boryl enamines or enamides. Fluorinated beta-aminoalkylboronic acids show no signs of degradation under ambient conditions. We present evidence for the involvement of chair-like motifs, favored over the acyclic forms by up to 1.7 +/- 0.1 kcal mol(-1) in water and held together by an amine-boronate hydrogen bond. Fluorinated beta-aminoalkylboronic acids are stable over a wide pH range and are characterized by a pK(a) of 3.4, which is the lowest of any alkylboronic acid.
引用
收藏
页码：16366 / 16371
页数：6
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